4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-3-en-1-ols, methods for their production and use as odorants

Abstract

The β,γ-unsaturated 2,2,3-trimethylcyclopent-3-enyl derivatives of formula I ##STR1## where R may be methyl, ethyl, propyl, isopropyl or butyl, the wavy line characterizes geometric isomers and the broken lines characterize stereoisomers. These compounds can be produced by reduction of the aldol condensation products of campholene aldehyde and aliphatic aldehydes using sodium borohydride at raised temperatures. The compounds can be used to individually or as a mixture with the relevant α,β-unsaturated alcohols as odorants or as an ingredient of perfume oils for cosmetic and technical consumer goods.

What is claimed is: 
     
       1. A compound having the formula I ##STR6## wherein R may be methyl, ethyl, propyl, isopropyl or butyl, the wavy line characterizes geometrical isomers and the broken lines characterize stereoisomers. 
     
     
       2. The compound of claim 1 wherein R is methyl. 
     
     
       3. The compound of claim 1 wherein R is ethyl. 
     
     
       4. The compound of claim 1 wherein R is propyl. 
     
     
       5. The compound of claim 1 wherein R is isopropyl. 
     
     
       6. A method for producing a compound as described in claim 1 which comprises: (a) condensing campholene aldehyde and R--CH 2  CHO, where R is defined as in claim 1, catalyzed by alkali hydroxides or alcoholates, and   (b) reducing in an alkaline environment the resulting α,β-unsaturated aldehydes using sodium borohydride at temperatures of 10°-80° C.   
     
     
       7. The method of claim 6 wherein the temperature in step (b) is 30°-60° C. 
     
     
       8. A perfume composition containing as an active perfume ingredient an amount of at least one compound of formula I according to claim 1 sufficient to impart sandalwood notes or woody undertones thereto. 
     
     
       9. The perfume composition of claim 8 wherein said active perfume ingredient comprises two or more compounds of formula I. 
     
     
       10. An artificial essential oil of sandalwood notes or woody undertones, which comprises having added thereto an amount of at least one compound of formula I according to claim 1 sufficient to impart sandalwood notes or woody undertones thereto. 
     
     
       11. The artificial essential oil of claim 10 wherein two or more compounds of formula I are added. 
     
     
       12. A process for augmenting or enhancing the aroma of a perfume or cologne composition comprising the step of adding to a perfume or cologne base an aroma augmenting or enhancing quantity of a product containing at least one compound having the structure ##STR7## wherein R may be methyl, ethyl, propyl, isopropyl or butyl, the wavy line characterizes geometrical isomers and the borken lines characterize stereoisomers. 
     
     
       13. The process of claim 12 wherein said product comprises two or more compounds of formula I. 
     
     
       14. The method of claim 6 which further comprises the step of (c) separating the compound from the resulting mixture by distillation.   
     
     
       15. The method of claim 14 wherein the temperature in step (b) is 30°-60° C. 
     
     
       16. A perfume composition containing as an active perfume ingredient an amount of a reduction mixture containing at least 1% of a compound of formula I according to claim 1 sufficient to impart sandalwood notes or woody undertones. 
     
     
       17. An artificial essential oil of sandalwood notes or woody undertones which comprises having added thereto an amount of a reduction mixture containing at least 1% of a compound of formula I according to claim 1 sufficient to impart sandalwood notes or woody undertones thereto.